The above question is not meant rhetorically. Like many home educating parents, I bought a copy of "Teach your own" years ago. I didn't think much of it and stuck it in a bookcase for the next decade or so. Recently, I fished it out and had a look through it. I had quite forgotten just how truly, monumentally awful it is!
For those unfamiliar with John Holt's books, his most popular ones consist of long, rambling, personal monologues, in which he reflects on his life as a teacher. He writes in a chatty, informal style, as though he were a favourite uncle giving you some friendly advice and his books are larded with a nuggets of homespun wisdom, usually presented in a toe curlingly twee way. He sprinkles homely anecdotes around and "Teach your own" also features many stories from parents who home educate according to his wise and good principles. I have chosen a couple of pages more or less at random; pages 143 and 144 in the chapter on Learning without Teaching. Let us look at the fathers whom he quotes approvingly and see if what they are saying is worth hearing.
The first man says, "It is not possible for an inquisitive child to delve deeply into dinosaurs without wondering about, and learning, how big they were (measurements), how many roamed a certain area (arithmetic), where they lived (geography), what happened to them (history) etc." This is, despite anything John Holt might believe to the contrary, a pretty fair load of nonsense. It is perfectly possibly to spend months being interested in dinosaurs, learn their Latin names and everything about them without once learning anything at all about geography or arithmetic.
I have known plenty of kids who become obsessed by dinosaurs. I have never met one who learned how many roamed in a certain area, let alone learned any arithmetic as a consequence. The reasons are obvious. Firstly, nobody has the remotest idea how many dinosaurs did roam in a certain area. Secondly, I have been looking in all the books in the local library about this aspect of dinosaurs. Not one has anything to say on the subject. Neither is any child likely to learn geography from studying dinosaurs. For one thing there were no continents at that time, just one large landmass called Pangaea. Fat lot of use that geography would be, unless you were planning to take a holiday in the Carboniferous Era. I couldn't find anything about this in any of the books in the kids' library either.
I don't believe for a moment that any child has ever learned any arithmetic as a result of reading about dinosaurs, or any geography either! On the next page, Holt quotes with apparent approval a father who has a four year old son, "He repeats and repeats things until he has them. We put him to bed at 9pm and often at 11pm we can hear him talking to himself as he goes over things he wants to get straight." Apparently the child counts to a hundred and twenty nine constantly and keeps obsessively muttering to himself about what he has learned that day. Now call me Mr. Old Fashioned, but if my four year old child were laying in the dark for two hours counting to a hundred and twenty nine and repeating everything he had learned that day, I would be seriously concerned. Sounds like an anxious kid who needs to relax.
The book is full of this sort of thing; pointless anecdotes which are supposed to present unschooling as a wonderful way of life. Perhaps the most irritating aspect of the book is the creepy and patronising way that Holt talks about children. Here he is on page 144 talking about visiting, " An eight year old friend and her mother". I can tell you now that grown up men don't really have eight year old girls as their friends. Presumably this is actually the daughter of a friend of his. To pretend that it is the child who is his friend is at best patronising and at worst, slightly sinister. I am on excellent terms with the young daughters of friends, but if I started referring to an eight year old girl as "My friend" it would raise a few eyebrows! He is always talking about "My young friends". Yuk.
Practically every page of this book has something to annoy one. How it ever came to be seen as a seminal work on home education is an absolute mystery.